In this talk, I will argue that certain historicist hermeneutics popular in American Studies have inhibited our ability to read the speculative thought that emerges from the quotidian archives of the 19th-century Atlantic world. I will make a case for what is often called “over-reading” those archives, in the interest of generating heterodox perspectives on the meaning of freedom from a century that is often understood to be in the thrall of classical liberalism. This talk will draw on the third part of my forthcoming book The Brink of Freedom, in which I ask what and how did freedom mean in the midst of three relatively unheralded and heterodox historical and textual flashpoints from the mid 19th-century Atlantic world: first, the black settler colonization of Liberia between 1820 and 1860; second, debates about the relationship between race and insanity in the U.S. census of 1840 and the Creole slave ship uprising of 1841; and third, a massive Maya uprising on the Yucatan peninsula that began in 1847 and came to be known as la Guerra de Castas, the Caste War.